KR930000511A - Crystalline Oxathiolane Derivatives - Google Patents

Crystalline Oxathiolane Derivatives Download PDF

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KR930000511A
KR930000511A KR1019920009537A KR920009537A KR930000511A KR 930000511 A KR930000511 A KR 930000511A KR 1019920009537 A KR1019920009537 A KR 1019920009537A KR 920009537 A KR920009537 A KR 920009537A KR 930000511 A KR930000511 A KR 930000511A
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crystalline form
hydroxymethyl
cis
amino
oxathiolan
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KR100244008B1 (en
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레이븐스크로프트 폴
고든 로버츠 토니
에반스 폴
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원본미기재
글락소 그룹 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV

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Abstract

내용 없음No content

Description

결정질 옥사티올란 유도체Crystalline Oxathiolane Derivatives

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

제1도는 침상 결정 형태(형태 Ⅰ)의 3TC를 나타내는 도면.1 is a diagram showing 3TC of a needle crystal form (Form I).

제2도는 양추형 결정 형태(형태Ⅱ)의 3TC를 나타내는 도면.FIG. 2 is a diagram showing 3TC of a cabbage crystal form (Form II). FIG.

제3도는 결정 형태 Ⅰ의 적외선 스펙트럼을 나타내는 도면.3 shows the infrared spectrum of Crystal Form I.

Claims (25)

결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in crystalline form. 양추형 결정 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in the form of a pepper crystal. 제1항 또는 제2항에 있어서, 융점이 170℃이상인 결정질 형태.The crystalline form of claim 1, wherein the melting point is at least 170 ° C. 4. 제1항 내지 3항중 어느 한 항에 있어서, 융점이 177 내지 178℃인 결정질 형태.The crystalline form according to any one of claims 1 to 3, wherein the melting point is from 177 to 178 ° C. 제1항 내지 4항중 어느 한 항에 있어서, 적외선 스펙트럼의 920및 850파수에서 흡수띠를 갖는 결정질 형태.The crystalline form of claim 1, wherein the crystalline form has an absorption band at 920 and 850 waves of the infrared spectrum. 제1항 내지 5항중 어느 한 항에 있어서, 적외선 스펙트럼의 1110파수에서 흡수띠가 없는 결정질 형태.The crystalline form of claim 1, wherein the crystalline form is absent in the 1110 wave of the infrared spectrum. 제1항 내지 6항중 어느 한 항에 있어서, 시차 주사 열량계 프로파일에서 177 내지 178℃에서 흡열이 개시되는 결정질 형태.The crystalline form of claim 1, wherein endotherm is initiated at 177 to 178 ° C. in the differential scanning calorimeter profile. 침상 결정 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in the form of acicular crystals. 제1항 또는 8항에 있어서, 융점이 약 130℃미만인 결정질 형태.The crystalline form of claim 1, wherein the melting point is less than about 130 ° C. 10. 제1항, 8항 또는 9항에 있어서, 융점이 124 내지 127℃인 결정질 형태.10. The crystalline form of claim 1, 8 or 9, wherein the melting point is from 124 to 127 ° C. 제1항 및 8항 내지 11항중 어느 한 항에 있어서, 시차 주사 열량계 프로파일에서 124 내지 127℃에서 흡열이 개시되는 결정질 형태.The crystalline form of claim 1, wherein the endotherm is initiated at 124-127 ° C. in the differential scanning calorimeter profile. 제1항 및 8항 내지 11항중 어느 한 항에 있어서, 적외선 스펙트럼의 약1110파수에서 흡수띠를 갖는 결정질 형태.The crystalline form of claim 1, wherein the crystalline form has an absorption band at about 1110 waves of the infrared spectrum. 제1도에 나타낸 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in crystalline form shown in FIG. 제2도에 나타낸 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in crystalline form shown in FIG. 제3도에 나타낸 적외선 스펙트럼을 갖는 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥시티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxythiola-5yl)-(1H) -pyrimidine-2 in crystalline form with an infrared spectrum shown in FIG. -On. 제4도에 나타낸 적외선 스펙트럼을 갖는 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidine-2 in crystalline form with an infrared spectrum shown in FIG. -On. 수용액으로부터 화합물을 결정화시키는 것으로 이루어진, 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온의 제조방법.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidine-2 in crystalline form, consisting of crystallizing the compound from an aqueous solution -Method of preparation of hot. 화합물의 수용액을 프로판-1-올과 함께 공비중류시키는 것으로 이루어진, 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온의 제조방법.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-in crystalline form, consisting of an azeotrope of an aqueous solution of the compound together with propan-1-ol Method for preparing (1H) -pyrimidin-2-one. 비수성 매질로부터 재결정화시키는 것으로 이루어진, 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온의 제조방법.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidine-2 in crystalline form, consisting of recrystallization from a non-aqueous medium -Method of preparation of hot. 제19항에 있어서, 비수성 매질이 C2-6알콜인 방법.20. The method of claim 19, wherein the non-aqueous medium is C 2-6 alcohol. 제20항 또는 21항에 있어서, 비수성 매질이 에탄올 및 공업용 메틸화 주정으로부터 선택되는 방법.22. The method of claim 20 or 21, wherein the non-aqueous medium is selected from ethanol and industrial methylation spirits. 침상 결정 형태의 화합물을 에탄올 또는 공업용 메틸화 주정 중에서 승온에서 숙성시키는 것으로 이루어진, 양추형 결정 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온의 제조방법.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolane- in the form of a cabbage crystal, consisting of aging a compound in the form of acicular crystals at elevated temperature in ethanol or industrial methylated spirit. 5 days)-(1H) -pyrimidin-2-one. 결정질 형태의 (-)-시스-4-아미노-1-(2-히드록시메틸-1,3-옥사티올란-5일)-(1H)-피리미딘-2-온 및 그의 제약상 허용되는 담체로 이루어진 약제.(-)-Cis-4-amino-1- (2-hydroxymethyl-1,3-oxathiolan-5yl)-(1H) -pyrimidin-2-one in crystalline form and a pharmaceutically acceptable carrier thereof Drug consisting of. 제23항에 있어서, 경구 투어용으로 적절한 형태의 약제.24. A medicament according to claim 23 in a form suitable for oral tours. 제23항 또는 24항에 있어서, 정제 또는 캡슐제 형태의 약제.The medicament according to claim 23 or 24 in the form of a tablet or capsule. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920009537A 1991-06-03 1992-06-02 Crystalline oxathiolane derivatives KR100244008B1 (en)

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Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4581979A (en) * 1983-07-01 1986-04-15 Automotive Products Plc Shipping and installation restraining clip for master cylinder input member
US6069252A (en) 1990-02-01 2000-05-30 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers
US5914331A (en) 1990-02-01 1999-06-22 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
US5444063A (en) * 1990-12-05 1995-08-22 Emory University Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
US6812233B1 (en) 1991-03-06 2004-11-02 Emory University Therapeutic nucleosides
US5817667A (en) * 1991-04-17 1998-10-06 University Of Georgia Research Foudation Compounds and methods for the treatment of cancer
GB9116601D0 (en) * 1991-08-01 1991-09-18 Iaf Biochem Int 1,3-oxathiolane nucleoside analogues
US6177435B1 (en) 1992-05-13 2001-01-23 Glaxo Wellcome Inc. Therapeutic combinations
US20020120130A1 (en) 1993-09-10 2002-08-29 Gilles Gosselin 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
US5587362A (en) * 1994-01-28 1996-12-24 Univ. Of Ga Research Foundation L-nucleosides
IL115156A (en) 1994-09-06 2000-07-16 Univ Georgia Pharmaceutical compositions for the treatment of cancer comprising 1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosines
US5703058A (en) * 1995-01-27 1997-12-30 Emory University Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent
US6391859B1 (en) 1995-01-27 2002-05-21 Emory University [5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides
US5808040A (en) * 1995-01-30 1998-09-15 Yale University L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides
AU722214B2 (en) 1995-06-07 2000-07-27 Centre National De La Recherche Scientifique (Cnrs) Nucleosides with anti-hepatitis B virus activity
US5914332A (en) * 1995-12-13 1999-06-22 Abbott Laboratories Retroviral protease inhibiting compounds
HUP9903249A3 (en) 1996-06-25 2001-04-28 Glaxo Group Ltd Combinations comprising vx478, zidovudine, ftc and/or 3tc for use in the treatment of hiv
US5753789A (en) * 1996-07-26 1998-05-19 Yale University Oligonucleotides containing L-nucleosides
TW536403B (en) * 1997-03-24 2003-06-11 Glaxo Group Ltd An ethanol and ethylenediaminetetraacetic acid free pharmaceutical composition comprising lamivudine and exhibiting antimicrobial preservative efficacy
US6436948B1 (en) 2000-03-03 2002-08-20 University Of Georgia Research Foundation Inc. Method for the treatment of psoriasis and genital warts
AU2002335489B2 (en) * 2001-03-01 2008-06-05 Abbott Laboratories Polymorphic and other crystalline forms of cis-FTC
CA2351049C (en) 2001-06-18 2007-03-13 Brantford Chemicals Inc. Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers
WO2003027106A1 (en) * 2001-09-25 2003-04-03 Cadila Healthcar Limited Process for the preparation of crystalline polymorph ii of lamivudine
AU2003217676B2 (en) 2002-02-22 2009-06-11 Takeda Pharmaceutical Company Limited Active agent delivery systems and methods for protecting and administering active agents
ES2286471T3 (en) * 2002-11-08 2007-12-01 Glaxo Group Limited PHARMACEUTICAL COMPOSITIONS ANTIVIRALES.
US20040224917A1 (en) 2003-01-14 2004-11-11 Gilead Sciences, Inc. Compositions and methods for combination antiviral therapy
EP1809662B1 (en) * 2004-11-10 2008-11-26 Novartis Vaccines and Diagnostics, Inc. Deamidated interferon-beta
US20060242012A1 (en) * 2005-04-22 2006-10-26 Sumit Agarwal Determining or scoring properties to solicit to join ad network using advertiser or aggregated advertiser interest
TWI471145B (en) 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc Unitary pharmaceutical dosage form
TWI375560B (en) 2005-06-13 2012-11-01 Gilead Sciences Inc Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same
DE602007009957D1 (en) * 2006-04-18 2010-12-02 Lupin Ltd NEW CRYSTALLINE FORM OF LAMIVUDIN
WO2009031026A2 (en) * 2007-09-06 2009-03-12 Combino Pharm, S.L. Novel pharmaceutical compositions
WO2009037538A2 (en) * 2007-09-17 2009-03-26 Aurobindo Pharma Ltd Process for the preparation of lamivudine form i
US20100324290A1 (en) * 2007-11-29 2010-12-23 Ranbaxy Laboratories Limited Crystalline form i of lamivudine and its preparation
CN101918416A (en) * 2007-11-29 2010-12-15 兰贝克赛实验室有限公司 1 of preparation replacement, the method for 3-oxathiolane, especially lamivudine and intermediate
EP2225232B1 (en) * 2007-11-29 2012-09-26 Ranbaxy Laboratories Limited Process for the preparation of substituted 1,3-oxathiolanes
WO2009127996A1 (en) * 2008-04-17 2009-10-22 Ranbaxy Laboratories Limited Novel crystalline form of lamivudine
US8536151B2 (en) * 2008-09-01 2013-09-17 Hetero Research Foundation Process for preparing lamivudine polymorph form
US20110288298A1 (en) * 2008-11-12 2011-11-24 Lupin Limited novel polymorph of emtricitabine and a process for preparing of the same
CN101531656B (en) * 2009-03-24 2010-12-08 福建广生堂药业有限公司 Lamivudine crystal form and preparation method thereof
CN101993439B (en) * 2009-03-24 2013-04-24 福建广生堂药业股份有限公司 Lamivudine crystal form and preparation method thereof
WO2010137027A1 (en) * 2009-05-27 2010-12-02 Hetero Research Foundation Solid oral dosage forms of lamivudine
EP2454244B1 (en) 2009-07-15 2013-06-26 Lupin Limited An improved process for preparation of efavirenz
EP2488516B1 (en) 2009-10-14 2015-04-01 Mylan Laboratories Limited Process for the preparation of lamivudine and novel salts in the manufacture thereof
ES2688925T3 (en) 2010-01-27 2018-11-07 Viiv Healthcare Company Antiviral treatment
US20120295930A1 (en) * 2010-02-03 2012-11-22 Shankar Rama Novel process for the preparation of cis-nucleoside derivative
AU2011215878A1 (en) * 2010-02-12 2012-08-09 Merck Sharp & Dohme Corp. Preparation of lamivudine Form I
CN114010776A (en) 2010-06-09 2022-02-08 疫苗技术股份有限公司 Therapeutic immunization of HIV-infected persons for enhancing antiretroviral therapy
US20130296562A1 (en) 2011-08-05 2013-11-07 Lupin Limited Stereoselective process for preparation of 1,3-oxathiolane nucleosides
WO2013168066A1 (en) 2012-05-05 2013-11-14 Lupin Limited An improved process for the manufacture of lamivudine form i.
CN114099454B (en) * 2020-08-31 2023-06-27 长春海悦药业股份有限公司 Lamivudine tablet and preparation method thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047407A (en) * 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
GB9009861D0 (en) * 1990-05-02 1990-06-27 Glaxo Group Ltd Chemical compounds
US5179104A (en) * 1990-12-05 1993-01-12 University Of Georgia Research Foundation, Inc. Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides
US5248776A (en) * 1990-12-05 1993-09-28 University Of Georgia Research Foundation, Inc. Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides

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